Structure-activity relationships of the estrogenic sesquiterpene ester ferutinin. Modification of the terpenoid core
(2004) In Journal of Natural Products 67(9). p.1557-1564- Abstract
- Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the a-face of the molecule proved detrimental. Taken... (More)
- Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the a-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/141154
- author
- Appendino, G ; Spagliardi, P ; Sterner, Olov LU and Milligan, S
- organization
- publishing date
- 2004
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Journal of Natural Products
- volume
- 67
- issue
- 9
- pages
- 1557 - 1564
- publisher
- The American Chemical Society (ACS)
- external identifiers
-
- pmid:15387659
- wos:000224187700023
- scopus:4644311704
- ISSN
- 0163-3864
- DOI
- 10.1021/np049796w
- language
- English
- LU publication?
- yes
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- d1f05737-d4eb-4889-acca-dd9a5c4678ba (old id 141154)
- date added to LUP
- 2016-04-01 17:11:54
- date last changed
- 2022-01-29 01:00:58
@article{d1f05737-d4eb-4889-acca-dd9a5c4678ba,
abstract = {{Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the a-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity.}},
author = {{Appendino, G and Spagliardi, P and Sterner, Olov and Milligan, S}},
issn = {{0163-3864}},
language = {{eng}},
number = {{9}},
pages = {{1557--1564}},
publisher = {{The American Chemical Society (ACS)}},
series = {{Journal of Natural Products}},
title = {{Structure-activity relationships of the estrogenic sesquiterpene ester ferutinin. Modification of the terpenoid core}},
url = {{http://dx.doi.org/10.1021/np049796w}},
doi = {{10.1021/np049796w}},
volume = {{67}},
year = {{2004}},
}